2-hydroxy-3, 3, 3-trichloro-1-aminopropane salt of penicillin



Patented Oct. 6, 1953 2,654,740

UNITED STATES PATENT OFFICE 2-HYDROXY3,3,3-TRICHLORO-1-AMINO- PROPANESALT OF PENICILLIN Harley W. Rhodehamel, Jr., Indianapolis, Ind.,assignor to Eli Lilly and Company, Indianapolis, Ind., a corporation ofIndiana N Drawing. Application February 13, 1952, Serial No. 271,430

2 Claims. (Cl. 260239.1) 1 2 This invention relates to a novelpenicillin salt Example 2 and the preparation thereof.

To an aqueous solution of 1 g. of the potassium I have dlscovered thatz'hydroxy'33s'tnchlo salt of penicillin G in 5 ml. of water is added aro-l-aminopropane or its salts can be combined with penicillin or itssalts by neutralization or 5 321 5335 223 ii gi 333 322 ii g g g gg gmetathetical reactions to form asparingly soluble mixture is cooled andstirred ocasionam; penicillin salt, thereby affording a means ofprewhereupon the Slightly soluble 2 hydroXy 3 P T- Penicillin fromSolution and p trichloro-l-aminopropane salt of penicillin G mg 9Moreovelj the novel pemcmm precipitates. The salt is separated, anddried in can be utilized therapeutically. A prolonged pem- 10 vacuocillin blood level can be secured upon administer- I claim? ing the saltparenterally by methods known to 1 2 hydroXy 3,33 trich1Om 1 aminopr0the medical art.

The following examples illustrate the preparaf g 52 2 5 23 512 $232231:SZ EES S tion of the novel salt of this invention: 15 g O1 EwamplelCl-L'l-CH-OHzNH: P To a solution of .3 g. of penicillin (e. g. a com- 01OH mercial mixture of the several penicillins) dissolved in 1.8 ml. ofamyl acetate are added .3 g. of The 2'hydmxy'3'33'tnchloro'l'ammopro'2-hydroxy-3,3,3-trichloro-l-aminopropane dispane salt of penicillinsolved in 15 m1. of amyl acetate. The mixture is HARLEY W. RHODEHAMEL,JR.

cooled and stirred occasionally whereupon the 2-hydrXY-3,3,3-trichloro--amimpropa?i Salt 0f References Cited in the fileof this patent penicillin precipitates. he sal is iso a ed as bydecantation or filtration, and dried in vacuo. UNITED STATES PATENTS Thesalt is represented by the following for- Number Name Date mula in whichP represents penicillin: 2,587,574 Young Feb. 26, 1952 O1 OTHERREFERENCES O1( JOHCH:N P British Report CMR-Br. 234 (PB 79,927), Dec.

01 OH 5, 1947, p. 3.

1. THE 2-HYDROXY-3,3,3-TRICHLORO-1-AMINOPROPANE SALT OF PENCILLIN REPRESENTED BY THE FOLLOWING FORMULA IN WHICH P REPRESENTS PENICILLIN: 